Back when I was in 9th grade, I purchased my first desktop computer. I did extra chores, mowed lawns, and shoveled snow to afford my dream machine. It came tricked out with a 900Mhz AMD Athlon Thunderbird CPU, 128MB of RAM, a GeForce 2 GPU, and a Plexdor CD burner. Housed in a bleak grey metal box, it was my pride and joy. Countless hours of Counter Strike, Total Annihilation, and Starcraft were played on that computer.

Despite my fond memories of that first computer, it was never the perfect performance machine. I had made many compromises to meet my meager budget, and the hardware was out of date less than 60 days after it arrived. So around that time, I vowed that someday I would buy myself the most ridiculous performance-intensive machine that could be had.

A while back I realized all of a sudden that I had more than enough cash to buy that no-holds-barred gaming machine. But desktop computers are no longer terribly practical. And I don't play Counter Strike in the evenings anymore. And my middling laptop runs the Adobe Creative Suite just fine. In fact, I spend most of my time in front of productivity and office applications at work, and in the evenings, I try to spend time away from the computer for the sake of variety. I have the cash, but I longer want that beast computer, and it's sad. When I explained my disappointment to a friend over lunch, he shrugged and said, "of course you wanted that computer, but dreams expire."

He was right. Since making my vow to buy an uber gaming machine, the dream had lost meaning for me, and like a mesofact, I had not updated my list of dreams.

This caused me to not only go through that list, but to re-evaluate how I pursue and value dreams. I have kept a bucket list for several years, but I here propose a short list of reasons why you shouldn't have one. Maybe you shouldn't even follow your dreams.

Destinations are boring.

As a society, we praise big dreams and tell kids to aspire to be astronauts. But as a society, we focus our dreams on destinations, not on the journeys that make them meaningful. I fell prey to this exact problem when we were founding my first startup. I wanted to build a successful startup. For three years, we worked hard, we got some lucky breaks, and these days Skritter is pretty darn successful. I have become an astronaut. And you know what? It's an empty victory, because as it turns out, what I really want is not to have a successful startup. What I want is to work hard on difficult problems with people I like. Notice the difference there: the first dream is a state, "success," the second dream is a process "work hard."

For all the glib discussion of life being a journey, not a destination, we overlook that fact when forming our deepest and most personal goals. Maybe you want to be a famous rapper, a skydiving instructor, or a polyglot. All of these are noble ambitions, but thinking about those dreams in terms of continuing actions rather than destinations makes them more meaningful. You don't want to be a rapper, you want to spend most of your time rapping in a studio. You don't want to be a skydiving instructor, you want to teach newbies how to enjoy their first jump. You don't want to be a polyglot, you want to spend time learning the nuances of dozens of languages.

Destinations are boring, and dreams that rely on them are hollow.

The exotic is kinda meh.

You know what sounds cool? Getting out of a Cleveland winter and working from Costa Rica for 2 months. The problem is that if you value a degree of consistency, recurring familial interaction, predictable diets, stable electricity and internet, reliable transportation, and a hundred other factors you probably take for granted, then it's actually not that cool. That was the story of my 2 months in Costa Rica.

Yet despite the disconnect, whenever I tell people about going to Costa Rica, most people said "I wish I could do that."

Daily life constrains choice sets to the degree that most people can't up and move to Costa Rica for 2 months. And for most people, that's a good thing. Dreams often take the form of overcoming the inertial forces that keep us grounded to the status quo. But it is precisely these forces that often make us happy. Many dreams are predicated on circumstances that by their very nature would make us unhappy.

Dreams made in a vacuum are meaningless.

I drive an extremely economical car and I've always dreamed of having a performance sports car. Recently I got the chance to test drive some exceptionally cool sports cars, and coming back to my little Suzuki Aerio was a relief. Why, you might ask, would I prefer my 1600cc putsy hatchback to a Mercedes Benz E55? I won't go into details, but in forming my dream about owning a sports car, I ignored all of my previous preferences. A Porsche looked cool, but in my daily life I prefer gas economy, reliability, and low insurance bills.

Dreamers are encouraged to think big, and that often implies "outside of our experience." This gets back to something Paul Graham suggests about finding what you love to do: if you aren't tinkering with computers in your free time, do you really want to be a programmer? If you didn't sacrifice to buy a sports car when you were 17, are you really invested in performance automobiles?

We often classify our unqualified aspirations as "dreams" and then foolishly work towards them. Daily experience is often a far better judge of what you will enjoy than a groundless idea of you got from society.

Summary

All of this might lead you to conclude that I think dreams are meaningless, but that's not the case. I think dreams are extremely important, but they often grossly misrepresent what people actually want from their life experience. I am still struggling to find a good way to pursue my own aspirations and would be interested to hear if anyone else has had luck better forming and achieving meaningful dreams.

Back in my junior year of college, I switched my major from Cinema Studies to Economics. I was sitting in the office of my favorite professor and adviser, a man who had his Economics degree from Harvard. I was asking about post-graduate options.

"I was thinking about maybe getting an MBA one day. Do Oberlin graduates stand a chance of getting into the Harvard MBA program?"

My adviser smiled in a good-humored way. "Honestly George, I don't know how anyone gets into the Harvard MBA program. I think you have to be magic to pull it off."

When I heard those words, my heart sank, but I took the advice to heart. Seven years and two startups later, I still vividly remember that conversation because it crystallized my understanding of how to pull off a seemingly impossible accomplishment: it's a magic trick.

Getting into the Harvard MBA program might embody a magic trick for most people, but magic tricks encompass anything that appears to be impossible on the surface. Retiring at the age of 30, traveling full time while working remotely, being a C-level executive at a Fortune 500 company, or knowing people of repute. All of these accomplishments work to confound explanation and increase the perceived importance of the speaker. After all, only 1 in a million spend our evenings rubbing shoulders with A-list celebrities and our days on the cover of a business magazine. It's unique, it's interesting, and it defies simple explanation.

But it's a mistake to write off such accomplishments as impossible. It's an even bigger mistake to write them off as unimportant or shallow.

I've learned the hard way that when you are an entrepreneur, it is extremely important to quickly impress people you meet. When all you have is a one-month-old company and a smile, people write you off unless you can quickly portray success. Maybe you didn't go to Harvard or MIT, but the more magic tricks you have under your belt, the more investors, customers, and peers will assume you can accomplish your next audacious goal. This is the first step in actually living your life like you want.

Which bring me to choosing magic tricks. I've used common examples above, but your achievements will be most impressive if they are your own. Maybe you want to start a nonprofit mentoring program and positively impact 1,000,000 kids. Maybe you want to make the next greatest search engine. Maybe you want to replace Netflix and bring the world a decent selection of on-demand movies. You need to define what you want to achieve, and then do it. The coolest thing about magic tricks is that they are cumulative: the more you've already done, the more people will believe you can accomplish the next one.

A few weeks back I was watching The Queen of Versailles, which is an independent documentary about billionaire timeshare mogul David Siegel and his quest to build the largest house in America. At the beginning of the movie, the director interviews Siegel about how Westgate Resorts got it's start. He talked about how he founded the company when he was young and naive, worked like hell, and managed to grow the company to billions in sales. What struck me about his description was how similar it is to the way I describe working on my first startup, with one critical difference: Skritter is a tiny bit less less profitable.

This got me thinking about the nature of effort vs reward. It's a common misconception among entrepreneurs that the harder you work, the more successful you become. This workaholic mentality causes people to sideline important aspects of their lives to maximize a perceived chance to make it big. I believe that effort and reward are correlated. If your goal is to become a millionaire, you are far more likely to reach your goal working very hard on a bunch of ventures than if you stay at a job that allows you to relax and coast. The age old motto "God helps those that help themselves," seems true.

But the the amount of reward you enjoy for your effort is randomly distributed. If it weren't, David Siegel of Westgate fame would have had to work a thousand times harder/longer than someone whose startup makes $1M/yr. Since that clearly isn't possible in a normal human lifespan, I'm forced to conclude that there is a big component of luck involved in the rewards anyone reaps from their efforts.

Having a deep understanding of that fact is important because it helps workaholics like me from over-investing in work. The truth is that I probably stand about the same chance of retiring early from a new venture whether I pace myself or work 100 hour weeks. Effort is important for success, but marginal effort is just that, and it seems a horrible waste to labor under the delusion that another few hours of work will be the difference between a decent living and early retirement.